My Passage to Womanhood, Volume 1

By Clare Penn

This autobiographical novel graphically details the rites of passage of a man, from being a teenager through to becoming the early-middle-aged female Clare, a journey that takes place under the influence of primarily dominant women. “I admit that I do enjoy the thrill of being outside a client’s hotel bedroom door or on a house front-door step, awaiting the door to open and seeing who has paid very good money for my services and use of my body for whatever fetish they may be into. ... However, the concept of sexual escorting for cash, the time with the client being what is paid for, and my love and submission to Elaine, I still need to mentally separate. She is still “encouraging” me in her usual ways to accept this as...I get to learn even more about fetish and submission, and ultimately pleasing her and other women.” Exploring the many facets of the femme domme world while telling the story of a submissive male seeking to satisfy a growing need to be a woman. Exotic LGBT and female-led fiction for connoisseurs of the authoritative woman.

• Language: English
• Publisher: Pink Flamingo Media LLC
• Release date: Dec 7, 2021
• ISBN: 9781954079458

Book preview

My Passage to Womanhood

One Man’s Exotic & Erotic Journey

From Masculinity to Femininity

Volume-One

By

Clare Penne

ISBN: 978-1-954079-45-8

A Pink Flamingo Ebook Publication

Copyright © 2021, All rights reserved

Smashwords Edition

Preface

This autobiographical novel is about the rites of passage of a man, from being a teenager through to becoming an early-middle-aged woman. It is primarily the story of his, or should I say her, sexual experiences and development as she, Clare, came into and under the influence of, primarily, dominant women. It explores many facets of the femme domme world and has a secondary theme of a man made submissive who not only craves a dominant woman but also seeks to satisfy a growing need to be a woman himself as he undergoes the long march towards realising his desires.

The novel slowly unfolds throughout with intricate detail of the surroundings in which Clare found herself. Her superb memory recall describes many of the finer points of the quality life she has led but, also, the reader will experience many moments of high sexual passion, frenzy, lust and romance that will convey themselves freshly to the most ardent lovers of our genre.

In this sense, this novel is not your average femme domme writing. It has been written in a sensitive, beautiful, descriptive style and you, the reader, will soon warm to Clare her friends and acquaintances, as well as the various stages and escapades of her life. And, apart from some wonderful times of sexual tension and joy, there are moments of sadness that emerge.

The style of the writing as such reflects the naivety and inexperience of being a teenager so as to capture the emotions rampant at that age and evolves as Clare develops his/her range of experiences as a submissive entwined in the world of feminine domination.

The beginning covers Clare’s early history, up to the time she reaches her late eighteens. This may sound very young but the author thought it important to include this, as it lays down the lasting foundation of her development in life, both as a submissive to dominant women, and in the sometimes-forced passage to becoming a woman herself.

The story involves Clare, her first friend, John, and then her first girlfriend, Hannah. Clare has commented that, indeed, Hannah has much to answer for in becoming what she has, and for the range of experiences that she was subjugated to by her, all those years back then.

Clare

Introduction

For those of you in the know, or who have done the research an interest in transgender and female domination issues demand, you will know that most of us start the long tortured route towards womanhood and submission to the fairer sex with a healthy, or unhealthy if you see it that way, interest in our mothers’ or sisters’ clothing.

This can start at a very young age in dressing in Mother’s, Aunt’s or an Au Pair’s lingerie, or by swapping clothes with our sisters or their friends. Alternatively, we can become more subversive at a slightly older age as we begin to link items, especially female underwear, to our sexual development and, in doing so, frequently a fascinating fetish is born. In practice, I prefer to call fetishes ‘interests with there being so many interesting aspects to them in our lives at large. And, frequently, there is a very present, dominant, power play involved from an older woman, be it a mother, sister, aunt or teacher.

I did not begin my transition to becoming a truly submissive transvestite in either way though.

I have two folk to thank for that in setting me on the long road, and they are my first real boyfriend and girlfriend, real in the sense of taking my virginity.

My book will explore these relationships, providing you, the reader, with the base for understanding the future domination of me by women who already knew their dominant personalities and how to manifest it in the expected of driven behaviour of their submissives.

The book, of course, also features those women who have discovered domination during their own journey in life and relationships as they began to comprehend their own sexuality and sexual requirements.

For those of you who may not enjoy male to male, may I suggest that you persist with the early story as, firstly, it shows a distinct phase of my transition and, secondly, because I am bi-sexual, like many of us submissives.

The major section of this story moves on to my first true girlfriend who introduced me to cross-dressing, living as a woman and gradually establishing her dominance over me, especially in psychological dominance to worship her.

Subsequent Parts will see me experience a deeper and deeper passage, resistance, and acceptance through modified and forced behaviour, into this hallowed and special world of Feminine Domination, that I have become so familiar with and largely cherish.

I am sitting here, completely dressed as a woman, at my computer at the insistence of my current domme girlfriend. We both write as a profession, being technical authors working mainly on science and engineering issues for various clients in a number of different industries. The type of writing embraces business communication articles such as in-house magazine articles, brochures, web literature and training manuals, along with the occasional placed newspaper item.

Both of us write some lighter material too, mainly for ourselves but occasionally for publication and sharing with a wider readership.

However, Elaine and her domme friends have challenged me and insisted that I capture and record my life’s sexual and transvestite experiences and history.

The purpose of this, she says, is so as to let those who are interested in Feminine Domination to read and know about another life story of a man who has wanted to be a woman and under the influence and control of a strong woman, and whether I wanted the domination or not.

The difference and interest for the reader comes from our interesting backgrounds and the gamut of experiences, tension, joy and love that comes from such relationships.

Indeed, I start the writing of this long tome under duress as Elaine has told me that if I do not put pen to paper then she will do so on my behalf. And if she has to do that, she will make it fully auto-biographical and name names so as to expose me totally to the world, so that family and past friends know about what may be considered by many as my lurid background.

I am sitting here, nicely dressed in a white Aubade Fleurs de Pommier lacy bra and matching Italien panties, my bra holding my now C cup breasts.

Over my lingerie, I am wearing a soft high quality white long sleeve shirt-cum-skirt with a bandeau effect around my waist and that sweeps up to my breast line. Over this, I have a grey calf-length cardigan as well as charcoal-coloured leggings and matching, plain pumps. I have one carat emerald-cut diamond studs in my ears and a pearl neck choker around my neck with my name on a platinum tag coming off the front of the choker. Off this, there is a second identical tag, engraved with Elaine’s Girl. In addition, I have an ankle and waist bracelet on, similarly tagged, as well as a Chanel pearl watch on my left wrist. My other wrist is sporting three silver bangles, off which there are two have provocative suggesting, silver, bondage loops.

As you may have realised, I am not your average Feminine Dominant submissive reduced to menial roles around the house and in continual service to my girlfriend.

If you think that, you may have seriously misjudged me; this is perhaps one of the reasons that Elaine and friends wish me to write this biography, as there are not many examples of up-market female-dominated submissives in this world of erotica.

Without wishing to sound arrogant, I am intellectually pretty smart and well-read. In my life, I have been fortunate to find folk that have respected this and used me in their businesses in some capacity.

It is true though that I retain certain key submissive tasks in function of my status as Elaine’s and my other domme’s personal girl. For example, apart from our professional writing, I am responsible for their laundry and, naturally, oral service in many capacities, as well as sexual services and so many other tasks at large.

I am also responsible for such service to her daughter, Isabelle, when she is at home and she to me as well as despite her young age, she does show signs of being able to dominate. As Elaine and our friends have said that, for many, being able to experience some submission makes one a better domme. Whether this is true, who knows?

Isabelle is being brought up in this lifestyle as well and we share many experiences, especially in the world where she is currently placed for undergoing her training and development, a similar path to what I experienced, a path however personalised for her profile, interests and well-being.

Isabelle is a 19 year old lovely girl, both to look at and to serve and a chip off the old block, like her beautiful mother in so many ways.

As Elaine has pointed out; if anything happens to her in the future, Isabelle will take always me on her as her partner, confidante and submissive, as that is how close we are, and we have other routes to attaining our satisfaction in the life-style.

We adore each other.

Yes, Isabelle is a lesbian; having experienced a not-so-pleasant introduction to men early in her young life and, more importantly, that relationships and love with women is certainly her sexual orientation. And yes, Elaine and Isabelle have crossed that taboo line of mother-daughter having sex together, so both of them have been, and are, heavily involved in my subjugation and service to them.

As to the house, Elaine and I both enjoy cooking and wine so that is very much leisure time for us. For the day-to-day household chores, she has employed a Thai house-keeper who has a live-in flat in one of her cottages on the premises. This arrangement between us all has freed us up for our professional work and for more play time. Indeed, Elaine, being poly-sexual, has now just started a relationship with the housekeeper, and I have taken on certain of her activities as a manifestation of my subservience and to allow them sex play time.

Although I do enjoy the life of living as a woman, there are certain hang-ups that I have had and do have with the domination of myself, what you, the reader, may term as a natural unwillingness that needs appropriate taming and discipline. My writing will explore some of these areas of reticence to obey as my biography slowly reveals itself.

At this time, though, many of these have been psychologically, or physically so, forced out of me so as to comply and submit to Elaine’s or my other dommes’ wants and orders, and thereby taking me deeper into submission. I still have such moments and thoughts of unwillingness. It is natural and goes with the patch where I need my Domme to make my decisions for me; I am a natural worrier when it comes to such affirmative action and, at worst it becomes procrastination.

Another area that may shock you, or maybe not, is that Elaine uses me as a high-class escort mainly, but not exclusively, to women. Most of these clients she knows or they have been recommended through to her.

Medical health is, of course, crucial and they have to meet her expectations and standards. However, they generally do have use of me as they see fit, though Elaine does provide certain guidance, particularly on the No-No’s. This activity is one that I still do baulk at and can find it uncomfortable and wish to rebel against, largely as I am probably more of a one woman person in character.

I admit that I do enjoy the thrill of being outside a client’s hotel bedroom door or on a house front-door step, awaiting the door to open and seeing who has paid very good money for my services and use of my body for whatever fetish they may be into. I have also travelled extensively in the UK, Europe and elsewhere for my services and that is largely an enjoyable activity, except when the airports have one of their frequent snafus.

However, the concept of sexual escorting for cash, the time with the client being what is paid for, and love and submission to Elaine, I still have to mentally separate.

She is still encouraging me in her usual ways to accept this as, apart from the not-inconsiderable income it brings into her house and to partners, I get to learn even more about fetish and submission, and ultimately to pleasing her and other women. I do find it hard to make this a willing and welcome activity and an expression of my submission to their want.

So, I am sitting here about to launch my biography to you, conservatively dressed but with a preparatory, large plug in me that Elaine has inserted in me. She is sitting opposite me in our study, closely watching me, and asking about my progress in writing this.

Following my scribblings today, the first of what will be a long, arduous and, hopefully, a pleasurable task, I am to dress in a soft, leather-laced corset and matching panties, and a sultry evening dress, as I am to head out this evening on such an engagement to have dinner with a 38 year old lawyer as her escort and then be available overnight to please her.

I already know that she is into serious restraint, bondage and flagellation of her submissive, along with oral, watersports and strap-sex. I know that I am in for a sore bottom tomorrow morning and to continue my writing will be an interesting experience.

Chapter One

Initiation & Sexuality

It is true that I grew up in a family dominated by women. I had an emotionally remote mother who was a single-child herself and besotted with her image and evening life, and four younger sisters; I still remain close to my eldest sister today. My father was always travelling with his work and, when at home, he was pre-occupied with his charity work and clubs, so he was always out in the evenings and weekends. He was a caring Dad though and a lot of fun when he had free time.

Overall, I must say that, despite some limitations, it was a good childhood I experienced. By the age of eight, I was shipped off to what is known as a Prep School in the United Kingdom, a preparatory school to get kids, from eight to thirteen years old, up to passing a horrendous series of exams known as Common Entrance to enter our Public School system.

To freak our American readers out, in true Brit form, a Public School is, in fact, a private school; the reason for this is that, for many of the older schools dating back to Mediaeval and Renaissance Age origins, they were schools for the then middle class children. To raise some additional funds for maintenance and continuity they said regular prayers to the dead in return for fees, hence a service to the Public. Sometimes they are referred to as Chantry Schools.

Less of this history lesson though, and more about me, as I am sure that you do not want a potted narration of English schooling systems. However, my prep school was fun; I was bright intellectually and quickly made my way through the years to spend some three years in the top form.

Sports-wise I was, I guess, average though I did show a good proficiency at cricket and golf, the latter of which was to stay with me. I had lots of friends and there was all the exuberance of youth as we had huge, dense woods to explore and set up tribes with